DoubleClick Dude Aces His Second Act

On Oct. 30, Kevin Ryan, chief executive officer of AlleyCorp, was changing into his Halloween costume in a taxi, zooming from midtown to the East Village. He was heading to a Halloween party for Gilt Groupe, one of six companies contained under the AlleyCorp umbrella; his costume, a Karl Lagerfeld getup, couldn’t have been more appropriate. The e-commerce site, launched last November, works like an online luxury sample sale: Mr. Ryan’s staff buys goodies at a discount from the likes of Diane von Furstenberg, Marc Jacobs and the real Mr. Lagerfeld, among others, and sells them on Gilt.com with up to 70 percent slashed off the retail price to their members. Mr. Ryan, 45, has a tall, thin frame topped with curls of salt-and-pepper hair. With his black jacket and dark sunglasses … voilà! He is fashion icon Mr. Lagerfeld (sans white pony tail).

Mr. Ryan is also an icon in the New York technology community. That same night, he had earlier attended a party at the W Hotel at Lexington and 50th Street to celebrate the Silicon Alley 100, a list of the most influential movers and shakers in the city’s digital and tech community. He helped assemble the list as co-founder and chairman of the digital business news site Silicon Alley Insider, which hosted the party along with the Founders Club, which brings together start-up CEOs and financiers. Mr. Ryan wasn’t eligible to be on the list, but if he had been, he may have snagged one of the top spots, snug among Fred Wilson, New York’s prominent venture capitalist, and Barry Diller, the Hollywood studio honcho turned Internet media mogul.

Mr. Ryan is best known as the former CEO of DoubleClick, the modest web start-up that morphed into the largest online ad-serving company in the world. In July 2005, the company was sold to the private-equity firm of Hellman & Friedman LLC for $1.1 billion. Google bought it last year for $3.1 billion, nearly double the size of their payout for YouTube.

For the past three years, Mr. Ryan and AlleyCorp’s chairman Dwight Merriman, who was a co-founder of DoubleClick, have been building six companies under the AlleyCorp umbrella. Besides Gilt Groupe and Silicon AlleyInsider, there’s Clusterstock, another news site (currently in beta form under the Silicon Alley Media branch) that covers the financial markets and is lead by former shamed Internet analyst Henry Blodget; Music Nation, a kind of YouTube for unsigned and independent musicians; Panther Express, which delivers high-quality Internet content on 425 media, entertainment, technology, gaming, news and Web 2.0 companies on servers around the world (Livejournal and the Obama campaign are just two of their clients); ShopWiki, a search engine that crawls online shopping sites, indexes deals and allows users to review the goods; and 10gen, a new platform designed to help developers build quick and easy Web applications. Mr. Ryan estimates that the companies will generate about $50 million in revenue this year.

Mr. Ryan and Mr. Merriman have found success by thinking up tech companies that take advantage of other industries headquartered in New York, from fashion and finance to media and Madison Avenue. Their AlleyCorp is an Internet incubator among various industries.

Last Friday, Mr. Ryan was sitting in a conference room at AlleyCorp’s headquarters on West 20th Street (each room is labeled as a New York neighborhood; we were sitting in “Wall Street”). It was Halloween, so candy and bags of Fun Dip were strewn haphazardly on the tops of cubicle walls, and fake spider webs stretched across the walls. Developers wore witch hats. Outside the conference room, there was a live, hairy spider in a glass case. His name was Charles.

Mr. Ryan doesn’t have his own office, just a desk at a cubicle among his 150 workers, where he has framed pictures of his three kids (they live on the Upper East Side). A copy of Inc. magazine sat by his keyboard.

Mr. Ryan was born in Milwaukee and grew up outside of Cleveland. His father worked for Caterpillar, the manufacturer of construction and industrial equipment, and his family traveled a lot. He spent first and second grade in Rome and spent half of his childhood in Geneva (which motivated him to later serve on the board of Human Rights Watch). He moved to New York in 1985, after graduating from Yale, and spent some years on Wall Street as an investment banker with Prudential Investment Corporation. He went to business school in France and had a brief stint working for EuroDisney.

Mr. Ryan speaks rapidly, in breathless, perfect sentences. Mr. Ryan seems well rehearsed in his rundown of AlleyCorp’s development, probably because he has repeated it so many times to prominent New Yorkers.

That morning, he had breakfast with a European venture capitalist to brainstorm about new companies. He had lunch with a former high-level employee from TheWall Street Journal to mine new ideas for Silicon Alley Insider. The day before, he had met with the head of MTV’s digital division to discuss the music industry. He also chatted up John Caplan, CEO of Ford Models, at the Silicon Alley 100 party. At the Gilt bash, Mr. Ryan was “on the dance floor until 1:30 in the morning,” he said.